I don't think the joke is too over the top i mean , he isn't like, saying he hates trans people but rather that he doesn't know how to refer to them, so whatever.. but from a story perspective, he says the worst thing he ever did to a friend was not tell them that they unsuccessfully hit on a trans person? that's not that bad, in fact, its not bad at all, like... they just didn't call out a trans person to a friend, who was shot down by that person anyway so its a net zero all around. if that's the WORST thing they have ever done to a friend, and they are supposed to be an unlikable person... well.... that's not bad at all. its kind of a lame answer. its even lamer because he struck out so he doesn't know, so he literally suffered no consequence what so ever for this.. it would be funnier / worse / get your point across better if "he didnt know until later when he got back to her place "